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Bi-Curious Personal Ad

I was 26 years old, and living in an apartment, just getting my career going after spending time in graduate school. I had always considered myself straight. I was never what you’d calla “babe magnet” and I was never real good at picking up women, but I wouldn’t say I was sexually deprived either. Through several one night stands and a few semi-long term girlfriends, I’d say I probably had at least as much sex as the average single male my age.

To make a long story short, I started wondering what it would be like to have sex with a guy. I wasn’t attracted to any particular guys, but the idea of gay sex was really starting to turn me on. I had never been homophobic, never disgusted by gay sex like a lot of people. I never really had any interest in it, but it didn’t gross me out.

So what does any bi-curious guy do that time, place a personal ad (the internet wasn’t that big yet).”Bi-Curious SWM 26 interested in meeting same for talking and maybe more.” The ad came with an “800” phone number for the people to reply to, so I didn’t have to give out my address or phone number.

The day the newspaper came out with my ad, I couldn’t believe what I had done. I said to myself “I can’t do this” and decided not to check my messages. But that night I masturbated fantasizing about sucking a guy’s dick.

So of course, a few days later I just had to call the number, and my hand was shaking as I dialed the phone. There were about 8 messages, the majority of which were from people who sounded like weirdo’s – “Oh, yeah man, I wanna suck your dick and if you’re not too bug I’ll let you fuck me. Call me, man.” Stuff like that. I didn’t feel comfortable contacting someone who seemed too into this lifestyle, so I ignored most of the messages.

There was on message that sounded just like me, kind of nervous and curious. “Hi, my name’s Anthony. I’m 24, 5’10” about 158 pounds. Average build, I guess. Brown hair. I’ve been kinda curious about what it’s like to be with a guy lately too. If you’re interested in talking, call me.” His build was a lot like mine, but I was about 15 pounds heavier. Not muscular but not fat either.

Hmmm, this guy at least didn’t freak me out. So I called him. He answered! What the hell am I supposed to say? To make a long story short, we were both very awkward in our conversation, but we managed to agree that we were both curious, couldn’t imagine ourselves falling “in love” with a guy or being a couple. We both were interested in kissing a guy, and oral sex. We decided to meet that Sunday afternoon (it was the only time he could get away from his girlfriend with no questions asked) at a restaurant near my apartment.

When I hung up, my first thought was “I can’t go through with this.” My second thought was “I’ve gotta whack off!” I jerked off thinking about him twice before I fell asleep that night.

So Sunday came. I waited in the lobby of the bar/restaurant. He was 20 minutes late and I figured he chickened out. I was sort of glad, actually. Then a guy walked in, came up to me and asked if I was Bob.

I said “Yes, are you Anthony?”

“Yeah, sorry I’m late” he said “I got a little lost.”

“I thought you chickened out,” I said. “I almost did.”

“Well, the thought did cross my mind.”

We both laughed at that and went into the bar and each had a beer. It was obviously not a good place to talk openly so we went back to my apartment. We sat on the couch, I put on the TV and we started talking – again awkwardly. A little talk about our sexual interests, but we mostly made small talk. After about 20 minutes I couldn’t take it anymore. If this was going to happen, if I wasn’t going to back out, something had to happen soon.

So I looked at him and said “Anthony, do you want to go into my room and fool around or something?” Boy was I smooth!

He took a deep breath, paused and said “Sure. By the way, my name is really Mike. I used Anthony so that if my girlfriend heard the message I could say it was a wrong number.” Smart guy I thought.

We went into my bedroom and then stopped, both looking at each other. I wasn’t sure what to do – should I get undressed, kiss him or what?

“I’m not really sure how to get started,” I said.

“Me either. Maybe we should just lay on the bed and hug each other first.”

So, we took our shoes off and laid on the bed next to each other, full clothed. I was looking at the ceiling, he had his eyes closed. I reached over and started stroking his arm. He reached over with his other hand and started stoking my arm too. I quickly started feeling his chest and latched onto a nipple and started rolling it in my hands. He moaned and tuned his head towards me, his eyes still closed. I looked at him and thought to myself, here it goes…and I kissed him!

I placed my lips on his and held them there. He stiffened up for a second then reached behind my head and pulled my face to him and opened his mouth. I immediately met his tongue. Again we were both nervous so not much tongue movement was occurring yet, just touching them to each other. I started tentatively probing with my tongue and he started to respond.

We made out like that for about 5 minutes, the whole time I’m thinking I can’t believe I’m doing this. I couldn’t believe that I started to get a hard on kissing a guy. This was unreal. Was he hard too?

I stopped playing with his chest and reached between his legs. I ran the palm of my hand over his crotch. He was hard alright! When I touched him there again he moaned. I did too.

I immediately broke the kiss and told him to sit up. He did. I took his shirt off and unbuckled his jeans. I took my shirt of and said “Are you sure you want to go further?” He looked away, but he said “Yes.” I started to slide his jeans off and saw he was wearing whit under wear – “tighty whitie’s” “Well this guy is definitely not a player I thought.

Since he was just laying on the bed I took my jeans off, and lad next to him. We were both naked. We started to kiss again. I rolled on top of him and we made out some more, grinding our pelvises together lightly.

“Do you want me to go down on you?” I asked him.

He looked me in the eyes and said “Yes!”

I slid down and got a look at his cock for the first time. It was maybe 5 inches long, and thin. I’m about 6″ and relatively thick – at least that’s what several girls had told me. Thankfully we were both circumcised – I don’t think I could have dealt with a foreskin.

I grabbed it and looked at it. I was on my knees, he was on his back and I bent over him. I kissed the head lightly. Oh my God, I can’t believe I’m doing this. I almost got scared and stopped, so I just closed my eyes and took the whole thing in my mouth. I never expected it to feel so soft and hard at the same time. It was almost spongy.

As soon as I had it in my mouth, Mike moaned. “Ooohhhh.” I stared sucking. I also started sing my hand on him, after all that’s the way I like it. I also started to caress his balls. I looked up and saw he had his eyes closed and his head back, hands clutching the bed.

“Is that ok Mike? Am I doing it right?” I asked.

“Uhh huh, yeah” was all he could say.

After a few more sucks I looked up at him again, still caressing his cock with one hand and his balls with the other and said “Do you like it?” He nodded. “It’s a guy sucking your dick, Mike. Can you believe that?”

“You’ve got to give me some too, Mike” I said as I turned my body so that we were in a 69 position. “C’mon Mike, try it.”

I felt his hand on my cock. He started slowly jerking it. I looked down at him and he had his eyes closed. I could tell he wasn’t sure if he could take my dick in his mouth. I slid my body closer to his, my dick closer to his mouth. He still didn’t take it.

“Mmmm, Mike that feels good. Suck me. C’mon” I said as I stopped sucking his dick and licked his balls. He moaned but still kept just jerking me off. I rolled on top of him, my dick was right over his mouth. I sucked his balls into my mouth and started rolling them with my tongue. He really started moaning now and when he opened his mouth I quickly thrust my dick into his mouth.

He froze. I froze. It seemed like an eternity, then I went back to giving him head. As I sucked, slowly his lips closed around my dick. I moaned. Then I felt his tongue circle the head of my cock.

“Mmmmm, Mike. Oh wow that feels so good” I said. He kept it up and started adding a little suction. “Mike that’s it feels good. Man, I can’t believe this I’m sucking a guy’s dick and he’s sucking mine. Mike am I a good cocksucker? Am I doing ok?”

He nodded his head as he kept sucking me. I rolled over and we were on our sides, each sucking and jerking each other off. I never moaned as much during sex in my life. Soon Mike started squirming a lot and slowly thrusting his hips. I stopped sucking for a second and put my finger in my mouth to wet it. I started sucking again and slid my finger toward his asshole. It was staring me right in my face. I started to play with it and the tried to insert it into his little hole.

He jerked back, dropped my dick from his mouth and yelled “No! Not there! No!”

I said “Ok” and I stopped and went back to sucking his dick with a vengeance. A girl fingered my asshole once while blowing me and it drove me out of my mind, so I figured he’d like it. I guess not.

Now I was on a mission. I wanted him to come, and I wanted it in my mouth. I sucked harder, and used my hand faster. He wasn’t sucking me any more, but I didn’t care. His hips started bucking and he pulled my head away from his dick! What the hell?

“I’m gonna come and I don’t want to come in your mouth.” he said, “Unless you want me to?”

“Why? Don’t you want to?” I asked.

“It’s just that my girlfriend won’t let me so I just figured…”

“Mike, I want you to come in my mouth. I want to feel what it’s like. If I go this far and don’t do that I’ll always be wondering what it’s like.”

“Ok!” he graoned as I started sucking him again. Now I had a goal. I wanted his come in my mouth as soon as possible. I was sucking him and stroking him. He was moaning like I couldn’t believe. His hips started bucking again. Now it was time. Once again I took my finger and this time I gave him no warning as I slid it up his asshole.

“Aaahhhh” he yelled “Oh my God, I’m cummmming”

Next I felt a spurt hit the back of my throat. Then another one, and another. It was coming faster than I could imagine. The taste was nice – I had tasted my own come after jerking off many times. I swallowed as fast as I could but some slid out of my mouth and down my cheeks. Now Mike was holding my head to his dick as I was sucking him and finger fucking his ass. I couldn’t have stopped if I wanted to, even though I didn’t.

With one last groan, his hips stopped bucking and his dick stopped spurting. I kept sucking and fingering his asshole till nothing was coming out any more. He started to go soft in my mouth and I stopped.

I sat up looked at him, the cum I couldn’t swallow running down my chin and said “Well, Mike, how was that? Was I better than your girlfriend?”

He just looked at me and said “Wow.”

I turned around, got close to him, took his head in my hands and kissed him. He was startled, I knew he didn’t want to kiss me with his come in my mouth, but I wanted him to taste it so I kept kissing and he soon started kissing back.

I broke our kiss, looked at him and said “Now it’s my turn to get off.”

Well, it was my turn to get off, but it wasn’t what I quite expected. I laid back and said “It’s your turn now Mike.” He looked at me nervously and lowered his head and started kissing, licking and sucking my dick. He was doing a pretty good job and a few moans escaped me. After about 2 minutes, I felt him stop sucking and he began jerking me off. At this point I knew he couldn’t go through with blowing me, but I had to get off, so I encouraged him to keep masturbating me. It only took another minute and I exploded – cum landed all over my stomach and his hands. I looked at him and said “Thanks.”

Mike then looked at me shyly, said “I think I have to go” and got out of the bed. We both silently went to the bathroom and cleaned ourselves off and got dressed. We silently walked to my door, and as he opened it he looked sheepishly at me and said “Thanks, that was great!”

As he walked to his car I said ‘Yeah, I thought it was great too!”

As I watched him drive off, I laughed to myself – this is what girls must feel like when guys get off and run. I wasn’t upset, nor did I feel jilted – hell, I got off and had fulfilled a fantasy while doing it. I still wondered what it would have been like to get fucked and more than a hand job would have been nice, but I was satisfied.

Later that night after I masturbated while replaying the episode in my head, I figured that was the last I’d hear of Mike. He seemed pretty uncomfortable when he left. I wasn’t sure what I would do. Again, I wasn’t “in love” with him, have “a crush” on him or any feeling like that, but I definitely would have like to go a little farther. However, I figured out of a bunch of responses to my ad I only got one person that didn’t sound like a freak and I wasn’t sure I wanted to press my luck – who knows, the next one could be a psychopath.

For the next week, I masturbated twice a day, most of the time about my session with Mike (although a few times the star of my fantasies was a woman I knew from the gym). Then one night while I was watching a ballgame on TV, the phone rang. When I answered, there was a pause and I began to think it was a telemarketer or a prank call. Then I heard “Uh, hi. This is Mike. Umm, do you remember me?”

I burst out laughing and said “Mike, don’t take this the wrong way, but I don’t think I’ll ever forget you.”

He laughed too. “Well,” he said, “I’m sorry for leaving in such a hurry last week. It’s just that I felt so weird, and wasn’t sure how to handle things.”

“Mike, I’m not sure how to handle things either. I still love girls. I don’t want to date you. I feel weird about having had sex with a guy, but I you made me come harder than I have in awhile, and I would definitely like to try it again, maybe even do more than last time.” “I feel the same way,” he said “But I also am not sure I can suck you off until you come, and I don’t want you to think I’m using you.”

“Mike, as long as you are willing to at least jerk me off like you did last time, we’ll be okay,” I said “but I would love it if you could suck me off. Don’t worry, you don’t have to swallow. I can get blow jobs from women, but I can’t suck their dicks or get fucked by them.”

We ended the conversation by setting a time to meet that Friday night. His girlfriend was going to be way that weekend so he made plans to spend the whole night if things really got hot.

Friday night came. My doorbell rang about 8 pm. I opened the door and Mike nervously said “Hi.” I had him come in and we talked a little. I smelled a little booze on his breath and figured he’d needed a little liquid courage, so I figured I’d help him by asking him if he wanted to get a few beers at a local bar. He agreed eagerly. I thought that if he was that nervous (hell I was still pretty nervous myself) and if we got started too early, he might leave in a hurry again. So I said “Okay, to the bar for a few beers it is. But I need to do something first.”

“Okay, what?” he said.

I leaned over to him and planted a kiss on him. He was shocked at first, but I didn’t care. I kept kissing and forced my tongue into his mouth. After he recovered from his surprise, he got into it and soon our tongues were dancing in and out of each others mouths. But I wasn’t looking for a make out session. As we kissed I unbuckled his jeans and pulled his zipper down. I release his long slim cock from his pants and jerked it twice. Then I broke the kiss and went right to it. I dropped to my knees, pulled his jeans and underwear down (blue bikinis this time). No gentle kissing, no licking, no tickling. I started sucking him as hard as I could.

He quickly put his hands on my head and groaned “Mmm, yeah”.

I jerked and sucked his cock like there was no tomorrow. I wanted to see how fast I could make him come. In about 2 minutes I found out, because he tensed up and spurted in my mouth. I swallowed as fast as I could – after all if we were going out I couldn’t dribble come all over his pants.

After I made sure there was no come left, I stood up and said “Okay, let’s go.”, so he got up, pulled up his pants and followed me out the door. We got in my car and drove silently to the bar – just about 10 minutes away. We went in – it was a neighborhood type bar. Dark, kind of noisy, lots of televisions, seats around the bar and a few tables and booths. It was about half full. I grabbed us a booth away from the busiest part of the bar, with a good view of a TV. The waitress came over and I ordered us each a beer and a shot of Jack Daniels. When she brought it, we downed the shots fast, then drank our beers as we watched a ballgame. We just hung out, talked about our jobs, sports, the asses on some of the girls in the bar (it turned out we both liked our women a little on the chunky side, with small tits, nice wide hips and round asses). We each had about 4 or 5 beers and 3 shots. I was used to drinking pretty heavily on the weekends, so I had a little buzz, but not too bad. Mike on the other hand was starting to get a little loaded and seemed like he was starting to relax. At 10 o’clock we decided to head back to my place.

As we were driving, Mike spoke up. “Um, what was it like when I came in your mouth? Did you like it?”

I looked at him and said “Mike, it really turned me on. It didn’t taste bad – I’ve tasted my own come before and it wasn’t any different.”

“Yeah, I guess I’ve tasted mine too. I was curious what it tasted like,’ he said.

“Well, all I can say is that the whole thing – kissing a guy, sucking his dick, swallowing his come, is a real turn on. I don’t think I’m gay, but I guess the fact that it’s so forbidden, it seems so dirty, that it turns me on – a lot!” I told him.

There was another minute or so of silence, then he spoke up again. “Um, you said the other night on the phone that you wanted to do what we did last time, and maybe more?”

“Yeah,” I said.

“Uh, what did you mean by more?”

I pulled into my driveway, parked the car and looked at him. “Mike, if I want to see what sex with a guy is like, I want to see what it’s all like.”

He looked at me and said “Does that mean…” and looked away.

I leaned over and kissed him lightly. “Mike, I want to know what it feels like to have you in my ass. I want you to fuck me. You game?”

His eyes almost popped out of his head. “I never did that before, my girlfriend would never let me.”

“I never did it either,” I said, “I’ve finger fucked a few girls’ assholes, but none would ever let me fuck them there. And as far as my ass, I had one girlfriend who would finger mine while she was blowing me, but that’s it. So, want to get out of the car and go inside?”

We got out of the car and went into my apartment. Mike stumbled a little bit on the way. I knew he was a little loaded and that suited me fine. Hell, if I encouraged women to get a buzz on in order to get into their pants, why not with a guy? We walked in the door and I told Mike to go into my bedroom, while I grabbed a bottle of booze.

When I walked into my room, Mike was standing at the foot of the bed, and had just taken his shirt off. I walked over to him, took his face in my hands and kissed him. This time he didn’t hesitate at all. As we continued to kiss, I ran my hands over his naked chest and started playing with his nipples. I then began kissing and nibbling his neck. I slowly worked my way down and began sucking and biting his nipples. My hands dropped to his ass and began kneading and stroking his ass over his pants. He was moaning and breathing heavily the whole time.

Then I unbuckled his pants and slid them down as I started kissing down his stomach. He stepped out of his jeans and kicked his shoes off. Soon I was on my knees in front of him, kissing his cock through his underwear, nibbling and teasing his cock and balls. I slowly slid his underwear down and licked the top of his dick. He shivered and groaned. I lightly kissed and licked all around his torso and thighs, avoiding his cock.

“C’mon Bob, don’t tease me,” he said. So I began sucking on his balls, nibbling them. First sucking one ball in my mouth, then the other. Stroking and caressing his thighs. Then up and down his cock 5 or 6 times. I could tell he was getting very excited. If I kept it up he wouldn’t last too much longer, but that’s not what I wanted.

I stopped sucking his dick and slowly spun him around so he was facing away from me. As he turned I nibbled and kissed his groin, his hip, his thigh. Then I began working on his ass cheeks. I wasn’t sure if I could go through with what I was planning, but I had had a few drinks too, so that was giving me courage. When I got him completely turned around, I placed my tongue at the top of his ass crack, and slowly ran it down. When I got to his little puckered asshole, he shivered, but I went past that area and down to his balls. Then I worked my way back up. I did this three times, and on the third time, when I got to his asshole I stopped. I kissed it, I tongued it like I was kissing his mouth. He really started moaning now. Then I went for it – I pierced his asshole with my tongue. “Unnnhhhh!” he moaned, “Bob, wow, Bob that feels so good.” I tongue fucked his asshole for a few minutes, then, when it was good and wet, I inserted my index finger. He jumped. I held him still and slowly started fucking it in and out. Then I added another finger. I could tell he wasn’t comfortable, but I didn’t really care. After a minute or two, he started fucking back against my fingers. He was getting into it a little.

That’s when I stopped. I stood up, put my arms around him from behind, kissed his neck and whispered in his ear, “I’ll finger or tongue your asshole later if you want me to, Mike. Do you want me to?”

He nodded, eyes closed.

“But first I need to get off, Mike. Will you help me?” Again, eyes closed, swaying as I nibbled and kissed his ear, he nodded yes.

I guided him to the bed and he laid down. I quickly got undressed and laid on top of him. We kissed, with my grinding my hips into him, rubbing my cock on his as he stroked my back and ass. “Mike, I need you to suck me. Will you do that for me? I won’t come in your mouth.”

He looked at me and nodded. I rolled off of him and onto my back. He started kissing his way down my chest and stomach. He grabbed my dick and began licking up and down. “Mmmm, Mike. That feels good.” He didn’t acknowledge me, but he kept kissing my dick and caressing my balls. With his other hand he started stroking my dick as he sucked. I was really starting to get turned on. I’m not usually very vocal during sex, but I couldn’t help moaning and groaning and encouraging him to keep going. As I felt myself getting closer I started stroking his head with both of my hands, helping control his rhythm.

“Mike, Mike, put your finger in my ass. Finger fuck my ass Mike.” I groaned. His sucking and stroking stopped for a split second. He hesitated then started working on me again, but made no move toward fingering my ass. “Mike, c’mon, please. Put your finger in my ass. You know it felt good when I did it to you.” He hesitated again, then stopped sucking me as he took his index finger, stuck it in his mouth to get it wet, then slowly inserted into my rectum. “Uunnnhh, oh God that feels good Mike.” He started slowly fucking my ass with his finger as he returned to blowing me. It wasn’t long before I was getting ready to come.

“Mike, use another finger. Put another one in,” I moaned as I gently held his head and controlled his rhythm.This time there was no hesitation. One his next out stroke with his finger, he added his middle finger and shoved them both up my ass. That sent me over the edge. As soon as I felt that second finger stretch my asshole, I started to come. With my first spurt he tried to pull away, but I held his head on my dick. After my second spurt hit his mouth, I felt him gag a little but I kept holding his head in place. With the third spurt he started swallowing as fast as he could. I couldn’t believe how hard and how much I came. I took my hands off of his head, but he kept sucking me until he had drained me completely, and cleaned up all the come that had dribbled out of his mouth. When he stopped, he laid on top of me and kissed me – hard! Our mouths clashed and our tongues danced. I could taste my come in his mouth. I knew that this was why he was kissing me, but I didn’t mind.

When he broke our kiss, I said “I’m sorry Mike, it was just a reaction, I couldn’t help it.”

He smiled and said “It’s okay. I wanted to do it but was afraid, so you just nudged me past my fears. Now I know what it’s like.”

I looked him in the eyes and said “Okay Mike, now it’s time for me to pay you back. I’ve been looking forward to this all week. I want you to fuck me. Do you want to fuck my ass?”

“Oh, God!” he said, “I always wanted to do that but my girlfriend would never let me.”

“Well, here’s your chance.” I told him, “You’ve just got to be patient and let me take control ok?”

“Sure thing” he said eagerly.

I rolled him off of me and reached over to my night table and grabbed a tube of KY I had bought earlier in the week. I bent over his and sucked his dick briefly, but I knew I wasn’t going to get it any harder than it was. I took a dab of KY and rubbed it all over his dick. The cool feeling of the gel made him moan. Once I had him all lubed up, I took some on my finger and worked it into my ass. Oh God did it feel good to do that. I put my leg across him and straddled his cock. I grabbed his dick as I slowly lowered myself down until his dick was pressed tight against my virgin ass. I leaned back and slowly his dick began to enter my ass. I felt the head of his cock begin to part my asshole and all of a sudden it slid in. The head of his dick was just inside my ass. I thought it would hurt but it didn’t. It was just a very warm, full feeling. Then I slowly lowered myself down until his cock was completely inside me. I couldn’t believe I was doing this.

Mike must have been looking at me and when my face grimaced and I gasped he asked “Are you okay? Should I stop? Does it hurt?”

“No”, I told him “it feels great. Oh, shit this feels good. I can’t believe I’m doing this. What does it feel like for you?”

I slowly started to rock back and forth on his cock, letting it almost slip out of me and then slowly sliding it back in. I was moaning like never before. The warm feeling that shot through my body as his dick slid out of me was incredible, and the full feeling when he was all the way in turned me on too. I slid up and down on his dick, grinding my ass into his pelvis, leaning forward occasionally to kiss him.

“Let’s change positions” I said as I let his dick slide out of my asshole. I got off him and got onto my hands and knees. He quickly got behind me and his cock slid easily back into me. Now he was in control and he started fucking in and out of me. I the feeling was incredible. I relinquished control and now he was doing the fucking, not me. He slowly increased his pace until he was hammering my ass as fast and as hard as he could. We were both grunting, moaning and sweating.

“Oh my God, this feels good! I think I’m going to come” he yelled. “Come in me. I want you to come in my ass. I want your come in me,” I yelled back. With one last thrust he came. I felt him spurt inside my ass. My ass suddenly felt warmer and very slippery. He kept thrusting until he stopped coming. I laid face down on my stomach and he laid on top of me, his dick still in my ass. In a few minutes we each began to catch our breath and his dick softened and slid out of my ass. I felt his come begin to ooze out of my stretched asshole and run down my ass and thighs. He rolled off of me and laid next to me. I told him to get up and go to the bathroom and wash his dick in case I wanted to suck it later. He did, and as he came back to my bedroom, saw the bottle of bourbon I had brought into the room earlier and took a very large swig. The he crawled into the bed and we both fell asleep.

After about an hour I woke up. My ass was a little sore and felt a little sticky. I turned to look at Mike and he was asleep on his back next to me. I looked down at his dick, and it was limp, but mine wasn’t. I was hard again. He wasn’t quite snoring, but he must have been sleeping deeply likely because of the booze. I was ready for more, so I leaned over and began playing with his nipples. They got hard immediately, but he didn’t respond other wise. After a few minutes of this, I slid down and began playing with his dick, stoking it, kissing it licking it. It stayed limp. I guess he wasn’t quite ready for another round yet. However, I didn’t need his dick for what I had planned.

I pushed his knees towards his chest and started nibbling his balls. Still no major reaction from him. Then I began tonguing his asshole. When my tongue entered him he moaned and placed his hands behind my head. He still didn’t open his eyes or speak though – he was still in a daze. I tongue fucked his asshole for awhile, then I grabbed the KY. I lubed my fingers and started finger fucking his ass. This brought more moans. As I was fingering his ass with one hand, I spread the KY over my dick with the other.

I had never fucked anyone’s ass and now here was my chance. I took my fingers out of his ass, got between his knees and pushed them towards his chest. I placed my cock on his tight little asshole. Then I leaned forward and kissed him. He groaned and kissed me back. I did this to distract him. Just as our making out started to get really hot I pushed my dick into his ass.

His eyes shot open. “No, no, no. I can’t. No. Stop,” he said as he tried to squirm from underneath me.

“Relax Mike, just relax. It’ll feel good. I promise,” I said.

“No, I can’t, no, this is too gay. I can’t let someone fuck me” he cried. He actually did start to cry a little bit. However, he was no longer fighting me. I leaned forward and kissed him again as I slowly withdrew my cock until only the tip was left in his ass. Then I slowly pushed it in as far as I could. By the third thrust, I was all the way in, and he was kissing me back. Two more strokes and he was grabbing my ass to make sure I went all the way in. I stopped kissing him and concentrated on fucking. My God, he was right.

The tightness was incredible. I had never felt anything like this before. “Fuck! Mike your ass is incredible. This feel soo good.”

“Keep fucking me” he grunted.

With his knees around his ears and his ankles on my shoulders I picked up the pace. Soon I couldn’t have slowed down if I had wanted to. I was ramming my cock up his tight ass as far as I could each stroke. The strokes got faster. Soon I felt a familiar feeling in my balls. I couldn’t stop it. I started to come in his ass. After 3 spurts, my dick slipped out and the rest of the come landed on his chest. I collapsed on top of him. After a minute I rolled off. “Are you okay?” I asked.

“Yeah,” he said “it was great. I can’t wait to tell my girlfriend about this.”

“What the hell?” I thought.

It turns out that Mike’s girlfriend knew about him and me getting together. They had been together for 4 years – she was 19, he was 24. He was her first and only boyfriend, and the only person she had ever had sex with. While Mike felt that he loved her, their sex life was not so great. Sex was almost always in the missionary position and didn’t last very long (I found out later that it was mostly because Mike was “quick on the trigger”, if you know what I mean). She would blow him, but wouldn’t let him come in her mouth. He hardly ever went down on her because he didn’t really enjoy it and she thought it was gross. They both loved making out and feeling each other up, but he didn’t think he ever made her come, except with his hand. He didn’t think she was frigid, she wasn’t a bitch and was willing to at least try different things, but sexually they just never meshed.

It was because of these problems with their sex life that Mike first began to think he might be interested in guys. He started reading gay/bisexual porn and even rented a few movies. Then one day she caught him whacking off to a magazine with guys doing guys and she freaked out! She was crying and yelling and couldn’t believe what was going on. Mike said he calmed her down and explained how he was feeling sexually, how he really loved her but he wanted to experiment, that what he learned about himself would help their sex life too. He said he had always been able to sweet talk her, and he also made it seem like it was her fault that he was doing this (this was my first inkling that maybe Mike wasn’t as nice a guy as he seemed). She agreed that he could experiment and that if he really liked it, she would try to go along with his ultimate fantasy of a threesome.

So, the week after Mike and I fucked each other, I met him and Jill at a bar near Mike’s apartment. They were standing at the bar and I was able to get a good look at her before they saw me. Jill was about 5’5″, a brunette with straight hair down a few inches past her shoulders. She was wearing a white silk blouse, unbuttoned to show what little cleavage she had – she was maybe a B-cup if she was lucky. I could see the hint of a black bra through her blouse. She also had on a black, pleated miniskirt that came down to just above her knee. While not fat, her middle was a little thick. She had rounded hips and a “bubble butt”. Her legs were gorgeous. (For Literotica readers, go to “Amateur Pictures” and look at “Sissy Exposed” to get an idea of what her body was like). She had a very pretty, very innocent face. Jill might not seem like a knock-out to guys who prefer supermodels and strippers, but I really get turned on by women with that type of look.

I walked up to them, introductions were made and we each had a drink. Jill looked very nervous and tense, and drank her drink quickly and was half way through another by the time Mike and I finished ours. I got the impression that even though Jill was not rude, she was not thrilled with the situation and was here just to make Mike happy. After some small talk, we left for Mike’s apartment.

When we got inside, Mike poured us all another drink as we sat on the couch. After Jill chugged her gin & tonic, Mike put his arm around her and started to kiss her. I took this as my cue and slid close to her and started stroking her hair. When she felt me start to kiss her neck, she froze.

“Wait,” she said as she broke their kiss. “No offense to you Bob, you seem nice, but I told Mike that I had to watch you two make it first before I would do anything with the both of you. I’m still not convinced Mike likes having sex with guys. I need to see it to believe it.”

“I understand,” I said. “No problem here. I always wondered what it would be like to have someone watch me have sex.” With that I leaned across her and started to kiss Mike. If she wanted a show, I was happy to give it to her. Jill was between us and Mike and I were swapping tongues just inches from her face. We broke the kiss and all three of us went into the bedroom.

Jill sat on a chair in the corner of the room, as Mike and I stood next to the bed, making out as we undressed each other. When we were both naked, we laid on the bed with me on top of him. I slid down and sucked on his nipples a bit, then licked my way down to his dick. I kissed the head, licked it and then sucked it into my mouth. Mike groaned.

From the corner I heard Jill say “I thought Mike said he liked giving blow jobs too, not just getting them.” In response to that, Mike pulled my hips toward him and I reversed positions so we were in a 69, with me on top. I like this position, because I can thrust my hips and “fuck” the other person’s mouth – it gives me a sense of control. As Mike and I licked and sucked and jerked each others cocks I took a peek over at Jill. She was sitting in the chair, her mouth hanging open, like she couldn’t believe what she was seeing. The expression on her face was alternating between concern (I guess from the fact that her boyfriend was getting better head than she ever gave – Mike was really moaning and writhing by now) and lust. Her right hand was in her lap, and her thighs were squeezed together, but she wasn’t playing with herself.

As much as I like getting head, I really wanted to fuck Mike’s ass. Maybe I just wanted to make him my “girl” in front of his girlfriend. I stopped fucking his mouth and really concentrated on getting him to come. It didn’t take long.

“Aaaahhhh, fuck, yeah” he groaned as he started to come. I swallowed the first part of his load, and then as a show for Jill I let the last 2 spurts dribble down my chin. I looked up at her with come running down my chin. At this point she was shocked, and after a few seconds of having our eyes locked, she blushed and turned away.

I got off Mike and turned around. I began to kiss him and as he licked his come off my chin, I heard Jill gasp “Oh my god!”

I turned and looked at her. “Do you want to see me fuck your boyfriend now, Jill? Do you want to see my dick in his ass? He likes it you know.”

She nodded and meekly said “Yes.” Between the booze and the sex, she appeared to be in a trance. She was rubbing her thighs together, squirming in her chair, but still not touching herself otherwise. Her skirt had ridden up a little, and I caught a glimpse of her black bikini panties, but otherwise she was still clothed.

I pushed Mike’s knees toward his chest, exposing his asshole to me. I lined up my dick with his little puckered hole and said “I’m going to fuck you now Mike. I can’t wait to have my dick buried deep in your ass. You like that don’t you?”

Mike nodded and mumbled “Mmmm hmmm.”

My dick was nice and wet from Mike’s blowjob, and his ass was lubed with the saliva that ran down his dick when I was giving him head. I looked over at Jill and asked her “Can you see this Jill? I want to make sure you can see my cock go into your boyfriend’s ass.” I never talked much during sex before, but I guess I was putting on a show for Jill.

She just nodded. Her face again showed total shock, with a bit of lust thrown in. With that I thrust my cock slowly into his ass. I didn’t stop until I was all the way in. “Mmmm, fuck that feels good,” I moaned. “Mike’s ass is so tight Jill. I can’t believe how it squeezes my cock.” I started slowly fuck him, and he started moaning. “I’m using your boyfriend’s ass as a pussy, Jill. Oh, man is he a good fuck!” As I continued to fuck Mike, I again looked over at Jill. By now she was breathing heavy and a few small moans slipped from her lips. I kept watching her get hot and horny, rubbing her thighs together but still afraid to touch herself – boy, she was really uptight. I kept looking back at Mike as I plowed his ass, his eyes closed with a look of pure pleasure on his face. He was moaning constantly. Looking from Jill to Mike and back again while I was fucking Mike’s hot, tight ass I couldn’t believe how turned on I was. I wasn’t going to last much longer.

With a load groan I started to come. “Jill, I’m coming in Mike’s ass. I’m filling your boyfriend with come. Oh fuck his ass feels soo good.” I looked at Jill our eyes met. I stared into her deep brown eyes as I came. I pounded my dick into his ass until I was spent. I leaned forward, kissed Mike, and my dick popped out of his ass. His eyes were closed, and he just laid there, almost asleep (you know how guys often get after sex). I, on the other hand, wasn’t done yet.

I got off the bed and walked over to Jill, who was still sitting on the chair in a daze. “It’s your turn now, Jill,” I said. “I want to see you and Mike fuck.” I took her by the hand and helped her up. When she stood, I started to unbutton her blouse. She didn’t help me, but she didn’t protest. After all the buttons were undone, I pulled the blouse from her skirt and slipped it off her shoulders. Her small breasts were being held up by a lacy black push up bra. I leaned forward and nibbled on her neck as I caressed her tits through her bra. Then I slid her skirt over her hips, until it dropped to the floor. Her panties were bikinis also black lace, matching the bra. I pulled her to me and ran my hands over her panty clad ass as I kissed and tongued her ear. Her breathing was definitely getting heavier, but there was no other response.

Then I undid her bra and let her breasts loose. Although they were small, they were firm and there was no sag to them (ah, the benefits of being just 20 years old!) I bent forward to kiss them as I slid my hand down over her panty covered pussy. When I sucked her nipples and rubbed her pussy a small moan escaped her lips. Not surprisingly, her panties were soaked. I slid my hand inside and discovered that her pussy was not shaved. I slid her panties down and stuck my index finger in her pussy. Even though she was sopping wet, it took some effort to slide my finger in – she was very tight. She bit her lower lip and moaned again.

After a minute or two of me sucking on her now rock hard nipples and fingering her sopping we pussy, I was ready for the next step. I stood up, kissed her lips lightly and said “Jill, I want to see you fuck Mike.” She just nodded absently. I led her over to the bed and helped her get on. “You have to get Mike hard again Jill, it looks like I wore him out. Suck his dick for me.” She leaned over and started kissing and licking his dick. He didn’t get hard, but she really wasn’t doing a very good job. No wonder he loved it so much when I blew him.

I took her hand in mine and placed it around his dick. I started helping her stroke it up and down. After a few strokes I removed my hand and she continued as I showed her. Mike’s dick was starting to stir. Then I told her to kiss the tip of it. She did. Next, I had her run her tongue around the tip a few times and then pit just the head in her mouth. After she sucked the head for a bit, he was completely hard.

“Jill, keep stroking him and take as much as his dick in your mouth as you can, “I encouraged her. She glanced at me nervously and then lowered her head and took about an inch more of his cock into her mouth. I figured she had to work her way up to swallowing more, but after about a minute I realized she wasn’t going any further. Because she was on her knees next to Mike, bending over him as she was blowing him, I had a perfect view of her big round gorgeous ass. I reached over and smacked it. She squealed and jumped, but she didn’t stop sucking him. “Dammit, Jill! You can fit more in your mouth. Do it! Swallow him, he’s not that big,” I growled at her as I put my hand behind her head and pushed it down further onto his dick.

She didn’t stop sucking him, but she resisted me. I pushed on her head harder and even though she still resisted, his cock went further into his mouth. I let up on her head and she came back to the tip of his dick. I pushed again. She still gave me resistance but went all the way to the bottom of his cock. I let up again, and she came up again. I paused to see if she would continue, but she didn’t. I began pushing up and down on her head. She resisted me the whole time, although to tell the truth I wasn’t pushing too hard. I guess she felt better about doing this “dirty” thing if she was being “forced”. Whatever. I never was dominant in the bedroom, never forced anyone (or even nagged or begged anyone) to do something they didn’t want to do, but this was turning me on.

Soon, Mike began to moan. I wanted to see them fuck, so I made her stop blowing him. I told Mike, “I want you to fuck her.” He sat up, kissed her and pushed her back on the bed. She laid back and spread her legs. He got on top of her, grabbed his dick, and guided it into her wet pussy. He started humping her. She just laid there. They didn’t kiss, didn’t make any noise, nothing. He just got on top of her, started humping as fast as he could and grunted as he came in about 30 seconds. He immediately rolled off of her and laid next to her breathing hard. She just laid there with her eyes closed and a frustrated look on her face. That was it? No wonder their sex life sucked! Mike was a jackrabbit, and she laid there like a dead fish.

So, watching them fuck didn’t turn me on like I thought it would. But, I had another idea. I spread her legs, and slipped a pillow under her ass. She looked worried. I kissed my way up her belly, and again sucked on those cute little breasts a bit. Soon I was laying on top of her. I went to kiss her, but she turned her head away. I grabbed her face, turned it toward me and said “Jill, do you want to come? Do you want to get off tonight or do you just want to lay there and let us use you?”

She couldn’t turn her head, but she averted her eyes from me. She meekly whispered “But I’ve never been able to…”

“Jill,” I said softly, “do you want to come?”

She closed her eyes and nodded.

“Then shut up, relax and work with me, okay?”

She nodded again. I kissed her again. She didn’t turn her head this time, but she didn’t kiss me back. After about 20 seconds I forced my tongue into her mouth. Again she didn’t respond right away, but soon we were tongue wrestling. After kissing for a minute, I reached between us, grabbed my dick and guided it to the entrance of her hairy cunt. I stopped kissing her, and looked down at her face. Her eyes were closed and she still looked nervous. As I shoved my dick all the way into her pussy, her eyes shot open and she gasped “Aaaahhh!”

I’m sure I’ve mentioned that I’m not hung like a porno star, but a few girls have told me I have a big cock, probably because I have more girth than most guys. No matter how I was hung, I was definitely a lot bigger than Mike, and considering that his was the only dick she had ever had, I filled her like she never had been filled before. God, she was tight, too! I don’t think I ever had a girl’s pussy grab my dick that tightly. I whispered into her ear “Does that feel good Jill?” She just nodded.

I began to slowly fuck her. Long, slow strokes. I would take my dick out until just the head was left in her cunt, then slowly push it all the way in until my pubic bone was grinding against her clit (that’s why I slipped the pillow under her ass before I got on top of her). When my cock was all the way in, I would rock my hips back and forth and side to side so I was really stimulating her clit. During this slow fucking and grinding I was nibbling on her neck and on her ear. I was whispering to her too. “Mmmm, Jill. You feel sooo good. Your pussy is so tight. I can’t believe how good you’re making my cock feel.” She began to breathe harder. “Jill baby, you’re so hot. I want to suck on your tits all day. I can feel how hard your nipples are, pressing into my chest.” I kept kissing her neck, blowing in her ear and whispering to her how hot she was and how good she was. I could tell she needed her ego built up if she was ever going to enjoy herself.

Even though she was breathing harder, she wasn’t making any noise, and she was still just laying there. I whispered to her to put her arms around me and hug me, stroke my back. She did. Then I reached down with both hands, grabbed her thighs and pulled the up towards my hips. “You’ve got the hottest legs I’ve ever seen, Jill. Wrap those sweet legs around me, baby.” She did that too. Then, as I would push my dick into her, I took my hands, placed them on her hips and rocked them toward me. Then as I pulled out, I rocked them away from me. After awhile, she started to let out little baby whimpers as I thust into her and pulled her hips to me. It took about 5 minutes before she finally started to rock her hips on her won as we were fucking. Finally, she had her legs wrapped around me and was fucking me back. At that point I began to pick up the pace, fucking her quicker and harder. If I hadn’t come in Mike’s ass already, I never would’ve lasted this long. Even though she didn’t know how to use it, her pussy was incredibly tight and was doing a number on my cock.

“I’m getting close to coming, baby. Are you? Am I helping you come?”

“Mmm hmm” she whispered softly.

I started fucking harder and faster. Our hips and bellies were slapping together. “Come with me Jill. I’m almost there. Let go baby, just let it go.”

Her whimpering got faster and louder. All of a sudden she wrapped her arms around me as tight as she could. Her back arched. Her hips thrust up against me one last time and stayed locked against me. “Aahh, aahh, aaaaaahhhhhhh”, she gasped.

When she started to come, that sent me over the edge. My dick erupted in her tight hot pussy. My come mixed with Mike’s. It seemed like I came forever. I couldn’t believe I came that much or that hard for my second come of the night. Wow. She had no clue what to do with it, but to me, Jill’s body was magic. I collapsed on her, both of us panting and trying to catch our breath. After a minute or so, I started to roll off of her, but she held me there briefly and whispered into my ear, “Thank you.”

As I got off her, I looked over at Mike. He was still dozing, but it looked like he was starting to come out of it. I looked at Jill and she was out of it too. I, on the other hand, still had some thing I wanted to accomplish.

I kissed Jill’s lips lightly. I moved down and kissed each light pink nipple. Then I started to nibble my way down her slightly rounded belly. I paused briefly to tongue her belly-button. I continued working my way down until I got to the light brown bush right above her pussy. It was neat and trimmed, but it definitely was a bush, not just wisps of hair or a landing strip. The hair was wet and sticky with come – Mike’s and mine. I always wanted to eat come out of a woman’s cunt, so here was my chance. I started nibbling her thighs and around Jill’s pussy. When I got to her lips, she stirred. She tried to push my head away, and murmured “No, it’s dirty,” but I just grabbed her hands and pushed them to the side. I looked over at Mike, who was now watching me start to eat his girlfriend.

“Mike, Mike, come here,” I said. He crawled over to me and I grabbed his dick. I put it in my mouth and gave it a few sucks. I wanted to get it good and wet. “I want you to fuck my ass, Mike. Do you want to?”

He nodded and moved to get behind me. While he was doing that, I scooped some our come off of Jill’s pussy, reached back and spread it all over my asshole to give us some extra lube. As I returned to lapping the come out of Jill’s pussy, I felt him grab my hips and position his cock right on my asshole. With my saliva on his dick and the come on my asshole, with one good push he slid in easily. I groaned and really started to working on Jill’s pussy, because at the rate Mike was banging away I knew he wouldn’t last long. Oh god was I feeling hot. Mike’s dick pounding my asshole felt so good, and our come mixed with the taste of Jill’s fresh young pussy was too much. The sensations attacking my body were driving me nuts!

I had licked up all the come I could from Jill’s pussy, bush and thighs. Next I went to work on her clit. When my tongue first touched it she gasped. I started sucking on it, licking it and biting it lightly. I started finger fucking her in rhythm with Mike fucking my ass. As I felt mike’s urgency pounding my ass increase, I saw Jill grab the sheet and mattress beside her and dig her fingers into it. Her back started to arch again.

“Uhhhh, Uhhhh, UUUUUnnnnnhhhhhh! She groaned as she came again.

“Ahhhh, fuck!” Mike screamed as he blew his load into my ass. I felt his dick convulse in my ass as it pumped another load of come. Jill’s pussy squeezed my tongue and fingers as her body convulsed in another orgasm,

In a few seconds, we all collapsed on the bed, spent. As I dozed off to sleep, Jill, whispered in my ear “Thank you, again.”

In the background I heard Mike say “Bob, you’re the best fuck I ever had.”